Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol

Low-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary...

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Main Authors: Roberta Bernini, Isabella Carastro, Francesca Santoni, Mariangela Clemente
Format: Article
Language:English
Published: MDPI AG 2019-06-01
Series:Antioxidants
Subjects:
Online Access:https://www.mdpi.com/2076-3921/8/6/174
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spelling doaj-d4f254d66c7d43cc9e29fe2903d367202020-11-25T00:42:43ZengMDPI AGAntioxidants2076-39212019-06-018617410.3390/antiox8060174antiox8060174Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and HydroxytyrosolRoberta Bernini0Isabella Carastro1Francesca Santoni2Mariangela Clemente3Department of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyLow-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary supplements and stabilizers of foods and cosmetics in non-aqueous media are limited for the hydrophilic character. With the aim to overcome this limitation, the paper describes a simple and low-cost procedure for the synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. The reactions were carried out under mild and green chemistry conditions, at room temperature, solubilizing the phenolic compounds in dimethyl carbonate, an eco-friendly solvent, and adding a little excess of the appropriate C2&#8722;C18 acyl chloride. The final products were isolated in good yields. Finally, according to the &#8220;circular economy&#8221; strategy, the procedure was applied to hydroxytyrosol-enriched extracts obtained by <i>Olea europaea</i> by-products to prepare a panel of lipophilic extracts that are useful for applications where solubility in lipid media is required.https://www.mdpi.com/2076-3921/8/6/174tyrosolhomovanillyl alcoholhydroxytyrosoldimethyl carbonatelipophilic alkyl estershydroxytyrosol-enriched extracts<i>Olea europaea</i>green chemistrycircular economy
collection DOAJ
language English
format Article
sources DOAJ
author Roberta Bernini
Isabella Carastro
Francesca Santoni
Mariangela Clemente
spellingShingle Roberta Bernini
Isabella Carastro
Francesca Santoni
Mariangela Clemente
Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
Antioxidants
tyrosol
homovanillyl alcohol
hydroxytyrosol
dimethyl carbonate
lipophilic alkyl esters
hydroxytyrosol-enriched extracts
<i>Olea europaea</i>
green chemistry
circular economy
author_facet Roberta Bernini
Isabella Carastro
Francesca Santoni
Mariangela Clemente
author_sort Roberta Bernini
title Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
title_short Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
title_full Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
title_fullStr Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
title_full_unstemmed Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
title_sort synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol
publisher MDPI AG
series Antioxidants
issn 2076-3921
publishDate 2019-06-01
description Low-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary supplements and stabilizers of foods and cosmetics in non-aqueous media are limited for the hydrophilic character. With the aim to overcome this limitation, the paper describes a simple and low-cost procedure for the synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. The reactions were carried out under mild and green chemistry conditions, at room temperature, solubilizing the phenolic compounds in dimethyl carbonate, an eco-friendly solvent, and adding a little excess of the appropriate C2&#8722;C18 acyl chloride. The final products were isolated in good yields. Finally, according to the &#8220;circular economy&#8221; strategy, the procedure was applied to hydroxytyrosol-enriched extracts obtained by <i>Olea europaea</i> by-products to prepare a panel of lipophilic extracts that are useful for applications where solubility in lipid media is required.
topic tyrosol
homovanillyl alcohol
hydroxytyrosol
dimethyl carbonate
lipophilic alkyl esters
hydroxytyrosol-enriched extracts
<i>Olea europaea</i>
green chemistry
circular economy
url https://www.mdpi.com/2076-3921/8/6/174
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AT isabellacarastro synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol
AT francescasantoni synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol
AT mariangelaclemente synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol
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